Slappy Cromwell is the stagename Rex Fortune, Adventure Seeker, a thespian and playwright. He was represented by Palido Domingo, and the two have had a long working relationship while working at Blood Island. After his gigs began to slow down, Slappy moved to Plunder Island, in hopes of resurrecting his flagging career. He considered himself tortured artist, and worried about the lack of audience interest in the old works of the Bard. In Curse of Monkey Island, Slappy was busy preparing for his stage production, SPEARE!, his personal take of classic Shakespearean works, which was being performed at the Long John Silver Center for the Performing Arts on Puerto Pollo.

He originally performed Shakespeare's plays as intended, but due to lack of interest from the vastly pirate population of the Tri-Island Area he attempted to rewrite the works into a fortyfive minute revue. He called it SPEARE!: A Theatrical Medley, however, the reworked script mostly had comedic elements including knock knock jokes and juggling acts. During his performance on Speare!, he worked with another actor, who was a large man wearing a pink dress, who played Juliet.

His agent, Palido Domingo, was responsible for the decision to change his name, believing that his birth name did not have star appeal. He had been with the actor on Blood Island. They most likely moved because the hotel there lost its popularity.

After the disastrous run of Speare, Slappy left his contract torn on the floor with a message scrawled on it, "To my agent, Palido Domingo: Palido, this is the worst booking you've given me since that fire-walking fiasco on Blood Island. I quit! Sincerely, Slappy Cromwell."